Dimethyl Sulfoxide → Mitoglitazone

HRID 1756628Notes

Reaction equation

HRID 1756628 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:26])[CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].C(O)C.C(OC(=O)C)(=O)C.CS(C)=O>O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:26])[CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:24][CH:25]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 702EthanolHCID 7918Acetic AnhydrideHCID 98642685-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

Product 1

HCID 10429242MitoglitazoneYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl]-2,4-thiazolidinedione. 1/2 C2H5OH (396 mg), acetic anhydride (1.5 ml) and dimethylsulfoxide (4 ml) was stirred at room temperature for 5 hours and then poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate and the solvent was distilled off. The oily residue was subjected to silica gel chromatography. A fraction eluted with chloroform-methanol (100:1, v/v) gave 5-[4-[2-(5-ethyl-2-pyridyl)-2-oxoethoxy]benzyl]-2,4-thiazolidinedione (75 mg, yield: 20%). This was recrystallized from ethyl acetate-hexane to obtain colorless prisms, m.p. 148°-149° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washA fraction eluted with chloroform-methanol (100:1

Sources & evidence

ORD record
ord-afdb7ea8915e42ada94ab982fa99b1d6
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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